AU2008337395B2 - Compositions containing at least one naphthoic acid derivative, benzoyl peroxide and at least one film-forming agent - Google Patents
Compositions containing at least one naphthoic acid derivative, benzoyl peroxide and at least one film-forming agent Download PDFInfo
- Publication number
- AU2008337395B2 AU2008337395B2 AU2008337395A AU2008337395A AU2008337395B2 AU 2008337395 B2 AU2008337395 B2 AU 2008337395B2 AU 2008337395 A AU2008337395 A AU 2008337395A AU 2008337395 A AU2008337395 A AU 2008337395A AU 2008337395 B2 AU2008337395 B2 AU 2008337395B2
- Authority
- AU
- Australia
- Prior art keywords
- phase
- acne
- film
- composition
- naphthoic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
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- 239000000203 mixture Substances 0.000 title claims abstract description 176
- 239000004342 Benzoyl peroxide Chemical group 0.000 title claims abstract description 102
- 235000019400 benzoyl peroxide Nutrition 0.000 title claims abstract description 102
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical group C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 title claims abstract description 89
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 60
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical group C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 title description 4
- 150000005209 naphthoic acids Chemical class 0.000 claims abstract description 41
- 239000002537 cosmetic Substances 0.000 claims abstract description 7
- 239000003814 drug Substances 0.000 claims abstract description 6
- 239000012071 phase Substances 0.000 claims description 74
- 206010000496 acne Diseases 0.000 claims description 70
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 63
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 55
- LZCDAPDGXCYOEH-UHFFFAOYSA-N adapalene Chemical compound C1=C(C(O)=O)C=CC2=CC(C3=CC=C(C(=C3)C34CC5CC(CC(C5)C3)C4)OC)=CC=C21 LZCDAPDGXCYOEH-UHFFFAOYSA-N 0.000 claims description 54
- 238000000034 method Methods 0.000 claims description 47
- 238000009472 formulation Methods 0.000 claims description 40
- 238000002360 preparation method Methods 0.000 claims description 36
- 239000003349 gelling agent Substances 0.000 claims description 29
- 239000013543 active substance Substances 0.000 claims description 28
- 230000008569 process Effects 0.000 claims description 28
- 239000006071 cream Substances 0.000 claims description 25
- 239000008213 purified water Substances 0.000 claims description 24
- 239000000126 substance Substances 0.000 claims description 24
- 239000003995 emulsifying agent Substances 0.000 claims description 23
- 239000006185 dispersion Substances 0.000 claims description 21
- 239000004480 active ingredient Substances 0.000 claims description 19
- 239000000499 gel Substances 0.000 claims description 19
- 238000002156 mixing Methods 0.000 claims description 19
- 229920002385 Sodium hyaluronate Polymers 0.000 claims description 18
- 229940010747 sodium hyaluronate Drugs 0.000 claims description 18
- YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(2s,3s,4s,5r,6r)-6-[(2s,3r,4r,5s,6r)-3-acetamido-2-[(2s,3s,4r,5r,6r)-6-[(2r,3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2- Chemical compound [Na+].CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 claims description 18
- 239000000080 wetting agent Substances 0.000 claims description 18
- 239000000839 emulsion Substances 0.000 claims description 17
- 239000008346 aqueous phase Substances 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 14
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 14
- 238000003756 stirring Methods 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 14
- 229920002401 polyacrylamide Polymers 0.000 claims description 13
- 239000002738 chelating agent Substances 0.000 claims description 12
- 239000000375 suspending agent Substances 0.000 claims description 12
- 239000003974 emollient agent Substances 0.000 claims description 11
- 239000003755 preservative agent Substances 0.000 claims description 11
- 239000003906 humectant Substances 0.000 claims description 10
- 235000019422 polyvinyl alcohol Nutrition 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- 238000000265 homogenisation Methods 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000012072 active phase Substances 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 208000035475 disorder Diseases 0.000 claims description 8
- 238000004945 emulsification Methods 0.000 claims description 8
- 230000003780 keratinization Effects 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 239000006210 lotion Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 230000024245 cell differentiation Effects 0.000 claims description 6
- 230000004663 cell proliferation Effects 0.000 claims description 6
- 238000006386 neutralization reaction Methods 0.000 claims description 6
- 206010000501 Acne conglobata Diseases 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims description 5
- 208000003911 Acne Keloid Diseases 0.000 claims description 4
- 206010051651 Dermatitis papillaris capillitii Diseases 0.000 claims description 4
- 210000001193 acne keloid Anatomy 0.000 claims description 4
- 230000007717 exclusion Effects 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 230000003472 neutralizing effect Effects 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 229920001296 polysiloxane Polymers 0.000 claims description 4
- 230000000306 recurrent effect Effects 0.000 claims description 4
- 201000004700 rosacea Diseases 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 claims description 3
- 206010000507 Acne infantile Diseases 0.000 claims description 3
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims description 3
- YTAHJIFKAKIKAV-XNMGPUDCSA-N [(1R)-3-morpholin-4-yl-1-phenylpropyl] N-[(3S)-2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-3-yl]carbamate Chemical compound O=C1[C@H](N=C(C2=C(N1)C=CC=C2)C1=CC=CC=C1)NC(O[C@H](CCN1CCOCC1)C1=CC=CC=C1)=O YTAHJIFKAKIKAV-XNMGPUDCSA-N 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- 230000002335 preservative effect Effects 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- TVIKMHRYESWHCR-UHFFFAOYSA-N 6-[3-(1-adamantyl)-4-decoxyphenyl]naphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C3=CC=C(C(=C3)C34CC5CC(CC(C5)C3)C4)OCCCCCCCCCC)=CC=C21 TVIKMHRYESWHCR-UHFFFAOYSA-N 0.000 claims description 2
- BCLMUIMQCLRLNV-UHFFFAOYSA-N 6-[3-(1-adamantyl)-4-hexoxyphenyl]naphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C3=CC=C(C(=C3)C34CC5CC(CC(C5)C3)C4)OCCCCCC)=CC=C21 BCLMUIMQCLRLNV-UHFFFAOYSA-N 0.000 claims description 2
- 230000032683 aging Effects 0.000 claims description 2
- 230000009931 harmful effect Effects 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 2
- 239000004530 micro-emulsion Substances 0.000 claims description 2
- 239000003094 microcapsule Substances 0.000 claims description 2
- 239000011859 microparticle Substances 0.000 claims description 2
- LDGIHZJOIQSHPB-UHFFFAOYSA-N CD437 Chemical compound C1C(C2)CC(C3)CC2CC13C1=CC(C2=CC3=CC=C(C=C3C=C2)C(=O)O)=CC=C1O LDGIHZJOIQSHPB-UHFFFAOYSA-N 0.000 claims 1
- 230000000699 topical effect Effects 0.000 abstract description 8
- 229960002916 adapalene Drugs 0.000 description 60
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 54
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 51
- 229920001983 poloxamer Polymers 0.000 description 23
- 239000004698 Polyethylene Substances 0.000 description 22
- -1 alkyl radical Chemical class 0.000 description 21
- 239000000047 product Substances 0.000 description 19
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 18
- 239000000470 constituent Substances 0.000 description 15
- 229920002125 Sokalan® Polymers 0.000 description 14
- 238000012512 characterization method Methods 0.000 description 14
- 238000000518 rheometry Methods 0.000 description 13
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 12
- 229920003083 Kollidon® VA64 Polymers 0.000 description 11
- 229940086555 cyclomethicone Drugs 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 9
- ONBWNNUYXGJKKD-UHFFFAOYSA-N 1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonic acid;sodium Chemical compound [Na].CCCCC(CC)COC(=O)CC(S(O)(=O)=O)C(=O)OCC(CC)CCCC ONBWNNUYXGJKKD-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 8
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 7
- 229920003082 Povidone K 90 Polymers 0.000 description 7
- 150000004676 glycans Chemical class 0.000 description 7
- 229920001282 polysaccharide Polymers 0.000 description 7
- 239000005017 polysaccharide Substances 0.000 description 7
- 229920000289 Polyquaternium Polymers 0.000 description 6
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 6
- 235000010980 cellulose Nutrition 0.000 description 6
- 229920002678 cellulose Polymers 0.000 description 6
- 229920001531 copovidone Polymers 0.000 description 6
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 6
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 6
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 6
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 5
- 230000015556 catabolic process Effects 0.000 description 5
- 238000006731 degradation reaction Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 150000004492 retinoid derivatives Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
- BANXPJUEBPWEOT-UHFFFAOYSA-N 2-methyl-Pentadecane Chemical compound CCCCCCCCCCCCCC(C)C BANXPJUEBPWEOT-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 229920003081 Povidone K 30 Polymers 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 229930006000 Sucrose Natural products 0.000 description 4
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 4
- NWGKJDSIEKMTRX-BFWOXRRGSA-N [(2r)-2-[(3r,4s)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)C1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-BFWOXRRGSA-N 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 230000002209 hydrophobic effect Effects 0.000 description 4
- 239000012875 nonionic emulsifier Substances 0.000 description 4
- BARWIPMJPCRCTP-CLFAGFIQSA-N oleyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC BARWIPMJPCRCTP-CLFAGFIQSA-N 0.000 description 4
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 4
- 229920000053 polysorbate 80 Polymers 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
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- 229960001727 tretinoin Drugs 0.000 description 4
- 229920001285 xanthan gum Polymers 0.000 description 4
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- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 3
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 3
- RMTFNDVZYPHUEF-XZBKPIIZSA-N 3-O-methyl-D-glucose Chemical compound O=C[C@H](O)[C@@H](OC)[C@H](O)[C@H](O)CO RMTFNDVZYPHUEF-XZBKPIIZSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 208000032544 Cicatrix Diseases 0.000 description 3
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- 229920003102 Methocel™ E4M Polymers 0.000 description 3
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- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 229920006243 acrylic copolymer Polymers 0.000 description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 230000001804 emulsifying effect Effects 0.000 description 3
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- 238000005259 measurement Methods 0.000 description 3
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 3
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 3
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- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
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- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 3
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- 229920002545 silicone oil Polymers 0.000 description 3
- 235000000346 sugar Nutrition 0.000 description 3
- HBXWUCXDUUJDRB-UHFFFAOYSA-N 1-octadecoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCCCC HBXWUCXDUUJDRB-UHFFFAOYSA-N 0.000 description 2
- 229940043268 2,2,4,4,6,8,8-heptamethylnonane Drugs 0.000 description 2
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 2
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 2
- 241001440269 Cutina Species 0.000 description 2
- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
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- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- HLLPKVARTYKIJB-MCQPFKOBSA-N [(2r,3s,4s,5r,6r)-6-[(2s,3s,4s,5r)-3,4-dihydroxy-2,5-bis(octadecanoyloxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl octadecanoate Chemical compound O[C@H]1[C@H](O)[C@@H](COC(=O)CCCCCCCCCCCCCCCCC)O[C@@]1(COC(=O)CCCCCCCCCCCCCCCCC)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](COC(=O)CCCCCCCCCCCCCCCCC)O1 HLLPKVARTYKIJB-MCQPFKOBSA-N 0.000 description 2
- GCSPRLPXTPMSTL-IBDNADADSA-N [(2s,3r,4s,5s,6r)-2-[(2s,3s,4s,5r)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[C@@]1([C@]2(CO)[C@H]([C@H](O)[C@@H](CO)O2)O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O GCSPRLPXTPMSTL-IBDNADADSA-N 0.000 description 2
- SZYSLWCAWVWFLT-UTGHZIEOSA-N [(2s,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)-2-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-2-yl]methyl octadecanoate Chemical compound O([C@@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@]1(COC(=O)CCCCCCCCCCCCCCCCC)O[C@H](CO)[C@@H](O)[C@@H]1O SZYSLWCAWVWFLT-UTGHZIEOSA-N 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- POJWUDADGALRAB-UHFFFAOYSA-N allantoin Chemical compound NC(=O)NC1NC(=O)NC1=O POJWUDADGALRAB-UHFFFAOYSA-N 0.000 description 2
- 239000010775 animal oil Substances 0.000 description 2
- 229960000686 benzalkonium chloride Drugs 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 2
- 229920001222 biopolymer Polymers 0.000 description 2
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| US476307P | 2007-11-30 | 2007-11-30 | |
| US61/004,763 | 2007-11-30 | ||
| PCT/FR2008/052169 WO2009077693A2 (fr) | 2007-11-30 | 2008-12-01 | Compositions comprenant au moins un derive de l'acide naphtoïque, du peroxyde de benzoyle et au moins un agent filmogene, leurs procedes de preparation, et leurs utilisations |
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| AU2008337395A1 AU2008337395A1 (en) | 2009-06-25 |
| AU2008337395B2 true AU2008337395B2 (en) | 2014-09-11 |
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| AU2008337395A Ceased AU2008337395B2 (en) | 2007-11-30 | 2008-12-01 | Compositions containing at least one naphthoic acid derivative, benzoyl peroxide and at least one film-forming agent |
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| US (2) | US8952066B2 (fr) |
| EP (2) | EP2224908B1 (fr) |
| JP (1) | JP5622582B2 (fr) |
| KR (1) | KR101538187B1 (fr) |
| CN (3) | CN101969923A (fr) |
| AU (1) | AU2008337395B2 (fr) |
| BR (1) | BRPI0819047A2 (fr) |
| CA (1) | CA2706655A1 (fr) |
| MX (1) | MX2010005516A (fr) |
| RU (2) | RU2526905C2 (fr) |
| WO (1) | WO2009077693A2 (fr) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7820186B2 (en) | 2001-12-21 | 2010-10-26 | Galderma Research & Development | Gel composition for once-daily treatment of common acne comprising a combination of benzoyl peroxide and adapalene and/or adapalene salt |
| DE102010022061A1 (de) * | 2010-05-31 | 2011-12-01 | Beiersdorf Ag | Polymerkombinationen für kosmetische Zubereitungen |
| ES2786103T3 (es) * | 2011-06-29 | 2020-10-08 | Sol Gel Tech Ltd | Formulaciones tópicas estabilizadas que contienen microcápsulas de núcleo-cubierta |
| CN104519857B (zh) * | 2012-05-14 | 2017-12-08 | 强生消费者公司 | 光彩组合物和使用方法 |
| FR2991171B1 (fr) | 2012-06-01 | 2014-05-23 | Galderma Res & Dev | Procede de preparation d'une composition dermatologique comprenant des oleosomes |
| FR2991174B1 (fr) * | 2012-06-01 | 2014-12-26 | Galderma Res & Dev | Composition dermatologique comprenant des oleosomes et des retinoides, son procede de preparation et son utilisation |
| DK2922528T3 (en) | 2012-11-20 | 2017-09-18 | Allergan Inc | TOPICAL DAPSON AND DAPSON / ADAPALEN COMPOSITIONS AND PROCEDURES FOR USE THEREOF |
| ES2861431T3 (es) * | 2012-11-27 | 2021-10-06 | Sol Gel Tech Ltd | Composiciones para el tratamiento de la rosácea |
| WO2017029665A1 (fr) * | 2015-08-20 | 2017-02-23 | Sol-Gel Technologies Ltd. | Compositions pour application topique comprenant du peroxyde de benzoyle et de l'adapalène |
| WO2017068673A1 (fr) * | 2015-10-21 | 2017-04-27 | マルホ株式会社 | Composition pharmaceutique pour la peau |
| CN106729722B (zh) * | 2016-11-21 | 2020-05-12 | 成都山信药业有限公司 | 一种制备稳定复方制剂的方法及复方制剂 |
| TR201720497A2 (tr) * | 2017-12-15 | 2019-07-22 | Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi | Adapalen, benzoi̇l peroksi̇t ve si̇katri̇zan grubundan bi̇r ajan i̇çeren kombi̇nasyon |
| TR201720506A2 (tr) * | 2017-12-15 | 2019-07-22 | Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi | Adapalen ve benzoi̇l peroksi̇t i̇çeren kombi̇nasyon |
| WO2019240290A1 (fr) * | 2018-06-16 | 2019-12-19 | ロート製薬株式会社 | Composition topique |
| CN109820748B (zh) * | 2019-03-25 | 2021-10-22 | 昆明蓝橙口腔医院有限责任公司 | 一种用于口腔产品的无水分基质及其应用 |
| CA3156674A1 (fr) * | 2019-10-10 | 2021-04-15 | Axcella Health Inc. | Formulations a volume reduit comprenant des entites acides amines |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030170196A1 (en) * | 2001-12-21 | 2003-09-11 | Sandrine Orsoni | Dermatological/cosmetic gels comprising at least one retinoid and benzoyl peroxide |
| WO2008006888A1 (fr) * | 2006-07-13 | 2008-01-17 | Galderma Research & Development | Adapalène et peroxyde de benzoyle combinés utilisés dans le traitement de lésions dues à l'acné |
| WO2008065306A1 (fr) * | 2006-11-28 | 2008-06-05 | Galderma Research & Development | Compositions comprenant du peroxyde de benzoyle, au moins un derive de l'acide naphtoïque et au moins un compose de type polymeres de polyurethane ou des derives de celui-ci, et leurs utilisations |
| WO2008087354A2 (fr) * | 2006-12-21 | 2008-07-24 | Galderma Research & Development | Gel creme comprenant au moins un retinoide et du péroxyde de benzoyle |
Family Cites Families (23)
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| CA347907A (fr) * | 1935-01-29 | The Union Drawn Steel Company | Filiere d'etirage | |
| EP0386960A3 (fr) * | 1989-03-07 | 1991-10-23 | American Cyanamid Company | Compositions pharmaceutiques utilisables comme véhicules de délivrance d'un médicament et/ou comme pansements pour blessures |
| CA2184828C (fr) * | 1994-03-28 | 2008-08-12 | Shanta M. Modak | Composition pour l'inactivation d'agents irritants dans des liquides |
| JP2935339B2 (ja) * | 1994-04-28 | 1999-08-16 | 日本化薬株式会社 | 外用消毒液 |
| JPH1017433A (ja) * | 1996-07-01 | 1998-01-20 | Pola Chem Ind Inc | 刺激防御剤及びそれを含有する刺激防御用の化粧料 |
| KR100631000B1 (ko) | 1997-11-07 | 2006-10-04 | 가부시끼가이샤 메디온 리서치 라보라토리즈 | 이산화탄소 함유 점성 제약 조성물 |
| TW393321B (en) * | 1997-11-28 | 2000-06-11 | Caleb Pharmaceuticals Inc | Acne/Blackhead removal strip |
| US6248168B1 (en) * | 1997-12-15 | 2001-06-19 | Tokyo Electron Limited | Spin coating apparatus including aging unit and solvent replacement unit |
| DE59913181D1 (de) | 1998-10-23 | 2006-04-27 | Aventis Pharma Sa | Zubereitungen zur topischen applikation von antiandrogen wirksamen substanzen |
| EP1446096A1 (fr) * | 2001-11-13 | 2004-08-18 | The Procter & Gamble Company | Compositions topiques contenant des enzymes stabilisees a l'aide d'inhibiteurs |
| FR2832311B1 (fr) * | 2001-11-21 | 2004-04-16 | Besins Int Belgique | Poudre filmogene, compositions la comprenant, leurs procedes de preparation et leurs utilisations |
| FR2833841B1 (fr) * | 2001-12-21 | 2005-07-22 | Galderma Res & Dev | Gel comprenant au moins un retinoide et du peroxyde de benzoyle |
| US20040161402A1 (en) * | 2003-02-18 | 2004-08-19 | The Procter & Gamble Company | Film-forming compositions for topical application |
| US8916050B2 (en) * | 2004-09-27 | 2014-12-23 | Special Water Patents B.V. | Methods and compositions for treatment of water |
| WO2006065991A2 (fr) * | 2004-12-17 | 2006-06-22 | Dr. Reddy's Laboratories Ltd. | Dispersion delivrant un agent actif |
| US7001592B1 (en) * | 2005-01-31 | 2006-02-21 | Aquea Scientific Corporation | Sunscreen compositions and methods of use |
| AR054805A1 (es) * | 2005-06-29 | 2007-07-18 | Stiefel Laboratories | Composiciones topicas para el tratamiento de la piel |
| US20070009472A1 (en) * | 2005-07-06 | 2007-01-11 | Niebauer Michael F | Personal care compositions comprising a non-binding thickener with a metal ion |
| DE102005036602A1 (de) * | 2005-08-01 | 2007-02-08 | Ge Bayer Silicones Gmbh & Co. Kg | Polyammonium-Polysiloxancopolymere |
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| MXPA06008988A (es) * | 2006-08-08 | 2008-02-07 | Fernando Ahumada Ayala | Preparaciones topicas antiacne que contienen retinoide (tazaroteno o adapaleno), antibiotico (fosfato de clindamicina) y/o queratolitico (peroxido de bonzoilo en microesponjas). |
| EP1967180A1 (fr) * | 2007-03-06 | 2008-09-10 | Almirall Hermal GmbH | Composition topique contenant un agoniste du recepteur de rétinoides |
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2008
- 2008-12-01 WO PCT/FR2008/052169 patent/WO2009077693A2/fr active Application Filing
- 2008-12-01 CA CA2706655A patent/CA2706655A1/fr not_active Abandoned
- 2008-12-01 KR KR1020107014446A patent/KR101538187B1/ko not_active IP Right Cessation
- 2008-12-01 CN CN2008801182974A patent/CN101969923A/zh active Pending
- 2008-12-01 CN CN201510593829.1A patent/CN105287484A/zh active Pending
- 2008-12-01 EP EP08863372.2A patent/EP2224908B1/fr active Active
- 2008-12-01 AU AU2008337395A patent/AU2008337395B2/en not_active Ceased
- 2008-12-01 BR BRPI0819047 patent/BRPI0819047A2/pt not_active IP Right Cessation
- 2008-12-01 RU RU2010126664/15A patent/RU2526905C2/ru not_active IP Right Cessation
- 2008-12-01 EP EP11167661.5A patent/EP2364692B1/fr active Active
- 2008-12-01 JP JP2010535441A patent/JP5622582B2/ja not_active Expired - Fee Related
- 2008-12-01 MX MX2010005516A patent/MX2010005516A/es active IP Right Grant
- 2008-12-01 CN CN201310085111.2A patent/CN103142460B/zh not_active Expired - Fee Related
-
2010
- 2010-05-27 US US12/788,865 patent/US8952066B2/en active Active
-
2014
- 2014-06-26 RU RU2014126090A patent/RU2014126090A/ru not_active Application Discontinuation
- 2014-12-11 US US14/567,865 patent/US20150216834A1/en not_active Abandoned
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|---|---|---|---|---|
| US20030170196A1 (en) * | 2001-12-21 | 2003-09-11 | Sandrine Orsoni | Dermatological/cosmetic gels comprising at least one retinoid and benzoyl peroxide |
| WO2008006888A1 (fr) * | 2006-07-13 | 2008-01-17 | Galderma Research & Development | Adapalène et peroxyde de benzoyle combinés utilisés dans le traitement de lésions dues à l'acné |
| WO2008065306A1 (fr) * | 2006-11-28 | 2008-06-05 | Galderma Research & Development | Compositions comprenant du peroxyde de benzoyle, au moins un derive de l'acide naphtoïque et au moins un compose de type polymeres de polyurethane ou des derives de celui-ci, et leurs utilisations |
| WO2008087354A2 (fr) * | 2006-12-21 | 2008-07-24 | Galderma Research & Development | Gel creme comprenant au moins un retinoide et du péroxyde de benzoyle |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2364692A3 (fr) | 2012-02-15 |
| CA2706655A1 (fr) | 2009-06-25 |
| RU2526905C2 (ru) | 2014-08-27 |
| EP2364692B1 (fr) | 2017-10-25 |
| KR101538187B1 (ko) | 2015-07-22 |
| RU2014126090A (ru) | 2016-01-27 |
| MX2010005516A (es) | 2010-06-02 |
| WO2009077693A2 (fr) | 2009-06-25 |
| BRPI0819047A2 (pt) | 2015-05-05 |
| CN101969923A (zh) | 2011-02-09 |
| JP5622582B2 (ja) | 2014-11-12 |
| CN103142460B (zh) | 2016-08-31 |
| EP2364692A2 (fr) | 2011-09-14 |
| RU2010126664A (ru) | 2012-01-10 |
| KR20100101123A (ko) | 2010-09-16 |
| CN103142460A (zh) | 2013-06-12 |
| EP2224908B1 (fr) | 2017-11-01 |
| US8952066B2 (en) | 2015-02-10 |
| US20110135584A1 (en) | 2011-06-09 |
| EP2224908A2 (fr) | 2010-09-08 |
| JP2011504923A (ja) | 2011-02-17 |
| WO2009077693A3 (fr) | 2009-11-05 |
| AU2008337395A1 (en) | 2009-06-25 |
| US20150216834A1 (en) | 2015-08-06 |
| CN105287484A (zh) | 2016-02-03 |
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| Date | Code | Title | Description |
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| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |